With NBA free agency nearly a week old, the most intriguing wild card remaining is Dwyane Wade. Although everybody assumed him returning to the Heat was merely a formality, contract negotiations have dragged on, and according to Miami Herald Heat columnist Ethan Skolnick, the relationship between Wade and the Heat is “at an all-time low.” So how the hell did it get there?

Wade became a free agent for the first time in 2010, and was ready to get paid. He had previously signed a max extension with the Heat that kicked in at the beginning of the 2007-08 season, but rookie extensions and full six-year max contracts are very different animals.

Instead, Pat Riley worked miracles and convinced both LeBron James and Chris Bosh to come to Miami. To make this happen, however, Wade had to leave $15 million on the table (as did James and Bosh) to make everything work with the salary cap. Their contracts were also slightly bigger—a couple hundred thousand dollars a year—meaning Wade wouldn’t be the highest paid player on the team.

Four years and two championships later, Miami’s Big Three all opted out of their contracts and became free agents. James returned to the Cleveland to Win One For The Land, and Bosh re-signed a monster five-year, $118 million max deal with the Heat. Wade, who had opted out to facilitate re-signing James, once again left money on the table, this time to help sign Bosh and free agent Luol Deng. He ultimately agreed to a two-year, $31.1 million contract, after having opted out of the final two years and $42 million left on his old, already below market deal.

A year later, the Heat and Wade danced again. He opted out of his two-year deal, and was reportedly looking for somewhere in the neighborhood of a three-year, $45–$50 million contract. Up to then, he’d left at least $20 million on the table over the past five seasons to give the Heat the flexibility to sign free agents, and thought the Heat would honor that sacrifice with a large financial commitment.

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But the Heat, seeing a declining 33-year-old with knee issues who hadn’t played 70 games in a season since 2010-11, didn’t want to commit long-term. In the end, the two sides settled on a one-year, $20 million deal, and tried to spin it as a win-win for both parties. But here’s what we wrote at the time:

So what happened here is Dwyane took a very big risk by going into a one-year deal with no cover fire, and had to precisely because the Heat think he’s too risky over that year to commit to the next.

Wade became a free agent once again this summer, after a year in which everything went as well as you could have reasonably expected. He played the most games in five seasons, was an All-Star, and helped lead the Heat to a narrow loss in the second round of the playoffs, all without the blood clot-sidelined Chris Bosh. He was relatively healthy and relatively good. And yet here he is, without the contract he surely believes he’s earned.

Look at things from Wade’s perspective. Over the past six years he’s earned $101 million, while a six-year max contract signed in 2010 would’ve earned him $126 million. He has been with the team for 13 years, helped it win three championships, was never the highest-paid guy on the team, willingly gave up tens of millions of dollars, and just turned in a high-level, if not top ten, season. With the exploding salary cap the Heat finally have plenty of space to offer Wade one last big free agent deal, the last he’s likely to get in his career.

But just a year after unsettled negotiations that resulted in a one-year contract, Wade foresaw another standoff. He didn’t participate in the team’s pursuit of Kevin Durant, as they made luring Durant and then re-signing Hassan Whiteside to a four-year, $98 million deal their priorities. When they finally turned to Wade, things rapidly deteriorated. From multiple reports, it seems that the Heat offered a contract in the neighborhood of two years and $40 million—which seems to be about fair value, ignoring extenuating circumstances—but Wade wants a guaranteed third year that the Heat are unwilling to offer.

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Yesterday Dan Le Batard detailed how the various years of James, Bosh, and Wade contract negotiations made for fraught relationships, an article that seems to have pissed both Wade and the Heat off. He is now going on a belated free agency roadshow, meeting with the Knicks and Bulls—premier teams without much salary cap space—but also the Nuggets and Bucks, usually free agency afterthoughts. It is unclear how serious of a threat Wade is to leave the Heat, or whether these meetings are merely intended to drive up Miami’s offer.

You don’t have to stretch to see things from either side’s perspective. Wade has been a loyal teammate and given up $25 million, and in the face of all sorts of marginal players getting big contracts, he feels he deserves one too. But the Heat, looking to build for the present and future, don’t want to hamstring themselves by giving Wade an above market contract just to reward loyalty, a la what the Lakers did with Kobe Bryant (though Wade is an infinitely more useful player at this point than Bryant was when he got his last big deal).

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But the biggest culprit in creating this mess, really, is the NBA’s salary cap. The reason this situation became so fraught in the first place is because in a salary capped environment, much of the team-building onus falls on players to take less money to fit in better teammates. Players are stuck in a no-win situation: if they refuse a salary cut they’re selfish multi-millionaires who don’t want to win, and if they sacrifice money they’re unfair ring-chasers breaking the fundamental precepts of the system.

It is also in some respects a prisoner’s dilemma, as if some stars take less money to help their teams, all stars have to or else they’re at a competitive disadvantage. Tim Duncan, Tony Parker, and Manu Ginobili have long played ball with the Spurs to improve the team. Dirk Nowitzki voluntarily took a ridiculous $15 million pay cut. Both Draymond Green and Klay Thompson signed for a bit less than the max, which helped grease the wheels for the eventual Durant signing. And all manner of veterans—David West is the latest notable—have signed minimum contracts to land with contending teams when they could’ve gotten much more.

Whatever happens with Wade and the Heat, there are sure to be plenty of hurt feelings and grievances to go around. Not because anyone is being a diva or an unsentimental bean counter, necessarily, but because the NBA’s current collective bargaining agreement and economic model make disputes like this one inevitable.